data_GB3
# 
_chem_comp.id                                    GB3 
_chem_comp.name                                  "(2R,3R,4S,5R)-2-({[(1R)-2-HYDROXY-1-PHENYLETHYL]AMINO}METHYL)-5-METHYLPYRROLIDINE-3,4-DIOL" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C14 H22 N2 O3" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2005-12-05 
_chem_comp.pdbx_modified_date                    2011-06-04 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        266.336 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     GB3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        2F1B 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
GB3 C15  C15  C 0 1 Y N N 27.481 68.306 12.096 3.083  0.931  0.586  C15  GB3 1  
GB3 C14  C14  C 0 1 Y N N 27.325 69.732 12.194 4.220  1.248  1.306  C14  GB3 2  
GB3 C13  C13  C 0 1 Y N N 28.319 70.548 12.778 5.223  0.310  1.460  C13  GB3 3  
GB3 C12  C12  C 0 1 Y N N 29.478 69.912 13.262 5.089  -0.946 0.899  C12  GB3 4  
GB3 C11  C11  C 0 1 Y N N 29.691 68.501 13.198 3.950  -1.264 0.183  C11  GB3 5  
GB3 C10  C10  C 0 1 Y N N 28.669 67.664 12.602 2.946  -0.327 0.029  C10  GB3 6  
GB3 C8   C8   C 0 1 N N R 28.802 66.133 12.526 1.704  -0.674 -0.752 C8   GB3 7  
GB3 C9   C9   C 0 1 N N N 28.944 65.502 13.928 1.811  -0.096 -2.164 C9   GB3 8  
GB3 O9   O9   O 0 1 N N N 28.982 64.092 13.769 2.061  1.309  -2.086 O9   GB3 9  
GB3 N7   N7   N 0 1 N N N 29.936 65.934 11.616 0.528  -0.107 -0.078 N7   GB3 10 
GB3 C6   C6   C 0 1 N N N 30.032 66.368 10.222 -0.623 -0.930 -0.475 C6   GB3 11 
GB3 C5   C5   C 0 1 N N R 31.152 65.787 9.365  -1.889 -0.392 0.194  C5   GB3 12 
GB3 N1   N1   N 0 1 N N N 30.795 65.912 7.940  -2.087 1.033  -0.148 N1   GB3 13 
GB3 C2   C2   C 0 1 N N R 31.273 67.182 7.406  -3.531 1.280  -0.312 C2   GB3 14 
GB3 C3   C3   C 0 1 N N S 32.669 67.190 7.995  -4.257 -0.062 -0.086 C3   GB3 15 
GB3 O3   O3   O 0 1 N N N 33.724 66.539 7.296  -4.724 -0.165 1.261  O3   GB3 16 
GB3 C4   C4   C 0 1 N N R 32.422 66.641 9.400  -3.143 -1.110 -0.363 C4   GB3 17 
GB3 O4   O4   O 0 1 N N N 33.474 65.768 9.786  -3.394 -2.326 0.345  O4   GB3 18 
GB3 C21  C21  C 0 1 N N N 31.338 67.179 5.899  -4.003 2.308  0.719  C21  GB3 19 
GB3 H15  H15  H 0 1 N N N 26.703 67.712 11.640 2.298  1.663  0.465  H15  GB3 20 
GB3 H14  H14  H 0 1 N N N 26.425 70.191 11.811 4.325  2.229  1.744  H14  GB3 21 
GB3 H13  H13  H 0 1 N N N 28.195 71.618 12.850 6.113  0.559  2.020  H13  GB3 22 
GB3 H12  H12  H 0 1 N N N 30.249 70.525 13.706 5.873  -1.679 1.020  H12  GB3 23 
GB3 H11  H11  H 0 1 N N N 30.599 68.065 13.587 3.844  -2.246 -0.256 H11  GB3 24 
GB3 H8   H8   H 0 1 N N N 27.911 65.617 12.140 1.603  -1.758 -0.810 H8   GB3 25 
GB3 H91  1H9  H 0 1 N N N 28.096 65.793 14.566 2.630  -0.581 -2.694 H91  GB3 26 
GB3 H92  2H9  H 0 1 N N N 29.871 65.852 14.406 0.878  -0.270 -2.700 H92  GB3 27 
GB3 HO9  HO9  H 0 1 N N N 28.990 63.877 12.844 2.121  1.633  -2.995 HO9  GB3 28 
GB3 HN7  HN7  H 0 1 N N N 30.695 66.403 12.068 0.380  0.809  -0.475 HN7  GB3 29 
GB3 H61  1H6  H 0 1 N N N 30.254 67.444 10.279 -0.457 -1.961 -0.164 H61  GB3 30 
GB3 H62  2H6  H 0 1 N N N 29.085 66.087 9.738  -0.740 -0.892 -1.558 H62  GB3 31 
GB3 H5   H5   H 0 1 N N N 31.299 64.766 9.746  -1.829 -0.518 1.275  H5   GB3 32 
GB3 HN1  HN1  H 0 1 N N N 31.215 65.162 7.429  -1.790 1.568  0.655  HN1  GB3 33 
GB3 H2   H2   H 0 1 N N N 30.638 68.047 7.649  -3.732 1.646  -1.319 H2   GB3 34 
GB3 H3   H3   H 0 1 N N N 33.091 68.205 7.946  -5.082 -0.182 -0.789 H3   GB3 35 
GB3 HO3  HO3  H 0 1 N N N 33.464 66.394 6.394  -5.094 -1.053 1.361  HO3  GB3 36 
GB3 H4   H4   H 0 1 N N N 32.346 67.488 10.098 -3.043 -1.297 -1.432 H4   GB3 37 
GB3 HO4  HO4  H 0 1 N N N 34.017 65.573 9.031  -4.184 -2.721 -0.050 HO4  GB3 38 
GB3 H211 1H21 H 0 0 N N N 31.872 66.280 5.557  -3.482 3.251  0.557  H211 GB3 39 
GB3 H212 2H21 H 0 0 N N N 31.872 68.076 5.553  -5.077 2.463  0.611  H212 GB3 40 
GB3 H213 3H21 H 0 0 N N N 30.318 67.178 5.487  -3.788 1.941  1.722  H213 GB3 41 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
GB3 C15 C14  DOUB Y N 1  
GB3 C15 C10  SING Y N 2  
GB3 C15 H15  SING N N 3  
GB3 C14 C13  SING Y N 4  
GB3 C14 H14  SING N N 5  
GB3 C13 C12  DOUB Y N 6  
GB3 C13 H13  SING N N 7  
GB3 C12 C11  SING Y N 8  
GB3 C12 H12  SING N N 9  
GB3 C11 C10  DOUB Y N 10 
GB3 C11 H11  SING N N 11 
GB3 C10 C8   SING N N 12 
GB3 C8  C9   SING N N 13 
GB3 C8  N7   SING N N 14 
GB3 C8  H8   SING N N 15 
GB3 C9  O9   SING N N 16 
GB3 C9  H91  SING N N 17 
GB3 C9  H92  SING N N 18 
GB3 O9  HO9  SING N N 19 
GB3 N7  C6   SING N N 20 
GB3 N7  HN7  SING N N 21 
GB3 C6  C5   SING N N 22 
GB3 C6  H61  SING N N 23 
GB3 C6  H62  SING N N 24 
GB3 C5  N1   SING N N 25 
GB3 C5  C4   SING N N 26 
GB3 C5  H5   SING N N 27 
GB3 N1  C2   SING N N 28 
GB3 N1  HN1  SING N N 29 
GB3 C2  C3   SING N N 30 
GB3 C2  C21  SING N N 31 
GB3 C2  H2   SING N N 32 
GB3 C3  O3   SING N N 33 
GB3 C3  C4   SING N N 34 
GB3 C3  H3   SING N N 35 
GB3 O3  HO3  SING N N 36 
GB3 C4  O4   SING N N 37 
GB3 C4  H4   SING N N 38 
GB3 O4  HO4  SING N N 39 
GB3 C21 H211 SING N N 40 
GB3 C21 H212 SING N N 41 
GB3 C21 H213 SING N N 42 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
GB3 SMILES           ACDLabs              10.04 "OC2C(NC(CNC(c1ccccc1)CO)C2O)C"                                                                                               
GB3 SMILES_CANONICAL CACTVS               3.341 "C[C@H]1N[C@H](CN[C@@H](CO)c2ccccc2)[C@@H](O)[C@H]1O"                                                                         
GB3 SMILES           CACTVS               3.341 "C[CH]1N[CH](CN[CH](CO)c2ccccc2)[CH](O)[CH]1O"                                                                                
GB3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "C[C@@H]1[C@@H]([C@@H]([C@H](N1)CN[C@@H](CO)c2ccccc2)O)O"                                                                     
GB3 SMILES           "OpenEye OEToolkits" 1.5.0 "CC1C(C(C(N1)CNC(CO)c2ccccc2)O)O"                                                                                             
GB3 InChI            InChI                1.03  "InChI=1S/C14H22N2O3/c1-9-13(18)14(19)11(16-9)7-15-12(8-17)10-5-3-2-4-6-10/h2-6,9,11-19H,7-8H2,1H3/t9-,11-,12+,13+,14-/m1/s1" 
GB3 InChIKey         InChI                1.03  KHLOMLBNZUMIHX-QKGWFMCXSA-N                                                                                                   
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
GB3 "SYSTEMATIC NAME" ACDLabs              10.04 "(2R,3R,4S,5R)-2-({[(1R)-2-hydroxy-1-phenylethyl]amino}methyl)-5-methylpyrrolidine-3,4-diol"   
GB3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "(2R,3R,4S,5R)-2-[[[(1R)-2-hydroxy-1-phenyl-ethyl]amino]methyl]-5-methyl-pyrrolidine-3,4-diol" 
# 
loop_
_pdbx_chem_comp_audit.comp_id 
_pdbx_chem_comp_audit.action_type 
_pdbx_chem_comp_audit.date 
_pdbx_chem_comp_audit.processing_site 
GB3 "Create component"  2005-12-05 RCSB 
GB3 "Modify descriptor" 2011-06-04 RCSB 
# 
